[5]cavitand

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: [5]cavitand
• 英文别名: 6,12,18,24,49-Pentamethyl-2,4,8,10,14,16,20,22,26,28-decaoxaundecacyclo[27.19.1.130,48.05,46.07,44.011,42.013,40.017,38.019,36.023,34.025,32]pentaconta-1(49),5,7(44),11,13(40),17(38),18,23(34),24,29,32,36,41,45,48(50)-pentadecaene；6,12,18,24,49-pentamethyl-2,4,8,10,14,16,20,22,26,28-decaoxaundecacyclo[27.19.1.130,48.05,46.07,44.011,42.013,40.017,38.019,36.023,34.025,32]pentaconta-1(49),5,7(44),11,13(40),17(38),18,23(34),24,29,32,36,41,45,48(50)-pentadecaene
• 化学式: C₄₅H₄₀O₁₀
• 分子量: 740.807
• InChiKey: VHCFXGQJXDARBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  55
• 可旋转键数：
  0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [5]cavitand 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 生成 6,12,18,24,49-Pentakis(bromomethyl)-2,4,8,10,14,16,20,22,26,28-decaoxaundecacyclo[27.19.1.130,48.05,46.07,44.011,42.013,40.017,38.019,36.023,34.025,32]pentaconta-1(49),5,7(44),11,13(40),17(38),18,23(34),24,29,32,36,41,45,48(50)-pentadecaene
  参考文献：
  名称：

  A new [4]carceplex, and a crystal structure and dynamic combinatorial chemistry of a [5]carceplex

  摘要：

  A new [4]carceplex (2-guest) is reported. It is composed of two cavitands linked by four disulfide bonds. It forms twistomers, which interconvert on a millisecond timescale. The energy barrier for interconversion of twistomers is guest-dependent. Formation of [4]carceplex 2-guest is template dependent. The selectivity in templates is flat relative to most previous related template work. Larger kin [5]carceplex 1.guests were reinvestigated. A crystal structure confirms the twist between the hemispherical cavitands. Use of a redox buffer allowed dynamic combinatorial chemistry to be performed between pairs of templates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.110
• 作为产物：
  描述：

  二乙氧基甲烷 、 溴氯甲烷 、 2,6-二羟基甲苯 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 1.0h， 以13.9%的产率得到[6]cavitand
  参考文献：
  名称：

  Expanding Cavitand Chemistry: The Preparation and Characterization of [n]Cavitands withn≥4

  摘要：

  The preparation of cavitands composed of 4, 5, 6, and 7 aromatic subunits ([n]cavitands, n = 4-7) is described. The simple, two-step synthetic procedure utilized readily available starting materials (2-methylresorcinol and diethoxymethane). The two cavitand products having 4 and 5 aromatic subunits exhibited highly symmetric cone conformations, while the larger cavitands (n = 6 and 7) adopt conformations of lower symmetry, H-1 NMR spectroscopic studies of [6]cavitand and [7]cavitand revealed that these hosts undergo exchange between equivalent conformations at room temperature. The departure of these two cavitands from cone conformations is related to steric crowding on their Ar-O-CH2-O-Ar bridges and is predicted by simple molecular mechanics calculations (MM2 force field). X-ray diffraction studies on single crystals of the [4]cavitand, [5]cavitand, and [6]cavitand hosts afforded additional experimental support for these conclusions.

  DOI：

  10.1002/1521-3765(20010417)7:8<1637::aid-chem16370>3.0.co;2-x

文献信息

• Synthesis and Characterization of a Disulfide-Linked <i>C</i>₅-Symmetric [5]Carceplex
  作者：Christoph Naumann、Samuel Place、John C. Sherman

  DOI：10.1021/ja017271+

  日期：2002.1.1

  The synthesis and characterization of the first disulfide-linked and C5-symmetric carceplex.(guests)2 using the recently described [5]cavitands as building blocks is reported. The solution behavior of the new carceplexes was explored by 1D NOSEY (EXSY) experiments. The disulfides have unusually high energy barriers to interconversion due to their cooperativity. The guests (2 DMF or 2 DMA) reside in an unusual orientation in parallel planes that are perpendicular to the principal axis of the host.
• Expanding Cavitand Chemistry: The Preparation and Characterization of [n]Cavitands withn≥4
  作者：Christoph Naumann、Esteban Román、Carlos Peinador、Tong Ren、Brian O. Patrick、Angel E. Kaifer、John C. Sherman

  DOI：10.1002/1521-3765(20010417)7:8<1637::aid-chem16370>3.0.co;2-x

  日期：2001.4.17

  The preparation of cavitands composed of 4, 5, 6, and 7 aromatic subunits ([n]cavitands, n = 4-7) is described. The simple, two-step synthetic procedure utilized readily available starting materials (2-methylresorcinol and diethoxymethane). The two cavitand products having 4 and 5 aromatic subunits exhibited highly symmetric cone conformations, while the larger cavitands (n = 6 and 7) adopt conformations of lower symmetry, H-1 NMR spectroscopic studies of [6]cavitand and [7]cavitand revealed that these hosts undergo exchange between equivalent conformations at room temperature. The departure of these two cavitands from cone conformations is related to steric crowding on their Ar-O-CH2-O-Ar bridges and is predicted by simple molecular mechanics calculations (MM2 force field). X-ray diffraction studies on single crystals of the [4]cavitand, [5]cavitand, and [6]cavitand hosts afforded additional experimental support for these conclusions.
• A new [4]carceplex, and a crystal structure and dynamic combinatorial chemistry of a [5]carceplex
  作者：Jianyu Sun、Brian O. Patrick、John C. Sherman

  DOI：10.1016/j.tet.2008.11.110

  日期：2009.8

  A new [4]carceplex (2-guest) is reported. It is composed of two cavitands linked by four disulfide bonds. It forms twistomers, which interconvert on a millisecond timescale. The energy barrier for interconversion of twistomers is guest-dependent. Formation of [4]carceplex 2-guest is template dependent. The selectivity in templates is flat relative to most previous related template work. Larger kin [5]carceplex 1.guests were reinvestigated. A crystal structure confirms the twist between the hemispherical cavitands. Use of a redox buffer allowed dynamic combinatorial chemistry to be performed between pairs of templates. (C) 2009 Elsevier Ltd. All rights reserved.